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Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf)2-catalyzed three-component cascade reaction of aldimines and two alkynes (IA2-coupling)

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Abstract

A zinc(II) triflate catalyzed three component synthesis of 1,6-dihydropyridines, involving aldimines, alkynes and electron-deficient dimethyl acetylenedicarboxylate (DMAD), in good to excellent yields has been described. Besides a range of different N-substituents, a variety of both aromatic and aliphatic alkynes could be used. The application of electron-deficient propiolates instead of DMAD resulted in regiospecific incorporation of the ester functionality on the 1,6-dihydropyridine ring. The reaction proceeds via a cascade reaction involving nucleophilic addition of the metal acetylide to the imine, followed by the addition of the intermediately formed propargylic amine to the electron-deficient alkyne and subsequent 6-endo dig cyclization.

Graphical abstract: Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf)2-catalyzed three-component cascade reaction of aldimines and two alkynes (IA2-coupling)

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Publication details

The article was received on 23 Jan 2018, accepted on 04 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00195B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf)2-catalyzed three-component cascade reaction of aldimines and two alkynes (IA2-coupling)

    S. A. Shehzadi, C. M. L. Vande Velde, A. Saeed and K. Abbaspour Tehrani, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00195B

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